


Don't Make Bets You Can't Win

by omgspnfanfiction



Category: Supernatural
Genre: Bets & Wagers, Blushing Dean Winchester, Confused Dean Winchester, Dean Winchester In Love, Dean gets played but he doesn't mind, Eating out, F/M, First Time, Fluff, Friends to Lovers, Getting Together, Half naked Dean Winchester, Idiots in Love, Love, Mild Smut, Mutual Pining, NSFW, NSFW GIF, Oral Sex, Played Dean Winchester, Pool & Billiards, Pool Table Sex, Risky, Secrets, Seduction, Shy Dean Winchester, Strip Games, Strip Pool, Stripping, Sweet Dean Winchester, Tricked, Tumblr, Vaginal Fingering, bad pool player, don't make bets, getting played, lying, naked reader, pussy licking, turned on
Language: English
Status: Completed
Published: 2019-04-19
Updated: 2019-04-19
Packaged: 2020-01-16 16:11:08
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 1
Words: 2,440
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18525019
Author URL: https://archiveofourown.org/users/omgspnfanfiction/pseuds/omgspnfanfiction
Summary: Dean teaches Y/n how to play pool and it somehow leads to strip pool





	Don't Make Bets You Can't Win

**Author's Note:**

> Sorry if the pool terms are wrong or nonexistent, I don’t know pool terminology.
> 
> Comments and kudos are appreciated!
> 
> If you ever want to chat or have suggestions go here, [My Tumblr](https://omgspnfanfiction.tumblr.com/)

“Hey Y/n, come out here I have to show you something” You heard Dean say through your door.

“Okay” You reply, letting out a quick sigh at having to leave your bed just to see what he wanted. 

Once you opened the door you were surprised at how he looked, he seemed so excited he was barely able to stand still. Your heart gave a little pulse at how adorable he looked. Dean didn’t give you a chance to say anything though, he just grabbed your hand and pulled you down the hallway, almost pulling your arm out from how fast he was trying to get there. He guided you to one of the several extra rooms the bunker had and stopped in front of it, letting you enter the room first. Inside there was a pool table, which was weird because you could’ve sworn there were random boxes in here last time you checked.

“Where did you get this?” You asked

“I found it for sale and bought it for you.” He said, eyes widening as he realized he said the last part out loud.

“For me?” You asked, shocked he would do something like this for you.

“Yeah, you told me you didn’t know how to play, so I thought it could be fun to teach you.” He said trying to act as if it was nothing, but you could see he was too excited and nervous about your reaction to be able to hide it. It made him look so innocent and young, reminding you of a kid on Christmas. You just couldn’t tell him the truth; it would crush him. So, you decided you’d lie and let him believe you had never played before, it would be easier and would avoid hurting him. Plus, this way you would also get to spend more time alone with him.

“Aww Dean, that’s so sweet of you. I don’t think anyone has ever done something like this for me before.” You say looking up at him and giving him a small peck on the cheek. As you pull back, you see his eyes are on the floor and his ears are turning red.

“It was nothing sweetheart, don’t mention it.” He waved you off, quickly changing the subject “Now are we going to play or what”

You rolled your eyes, classic Dean always changing the subject when things could get serious. That’s exactly why you weren’t together yet because he was too stubborn to admit he liked you in that way. But you couldn’t deny the way your heart skipped a beat at his shy demeanour or the fact that he bought you a pool table. You loved the idea of Dean being so close to you, so you nodded and grabbed a pool cue.

“Ok, but I’m going to suck at this game.” You say bending over to hit the ball, you aim, and the ball goes flying off the table, not touching a single ball. “See”

“Don’t worry sweetheart, I’m here to help.” Dean said grabbing the ball off the floor and leaning into your back to help aim the stick and shoot. The white ball breaking the balls and they all went different places but one managed to hit the solid into the hole.

“Oh my god, Dean! It went in!” You say excitedly, hugging him. He was smiling when you let go and moved around the table to take his turn, trying to act unaffected by your hug. His reaction made you bite your lip to hide the smile that wanted to form.

You continued to play for hours, you kept doing horribly but Dean still looked so happy to be spending all that time with you and being able to teach you something he was very skilled at. You didn’t care how bad you sucked, it was all worth it to see Dean smile like that.

\----

“Come on Dean! Let’s play strip pool” You say trying to convince Dean in your drunken stupor. Both of you had decided to get drunk after the last hunt to let loose. It had been a tough one but now you were bored and wanted to do something. Both of you were quite drunk already and you thought it was a good idea to play pool again, having been playing several times with Dean the past few weeks since he bought it. This time though your drunk mind believed strip pool would be more fun and exciting than just regular pool. Even though you had not gotten any better in any way at playing.

“Ok princess” Dean agreed, his drunk mind also thinking it was a great idea.

Dean was winning, obviously, being drunk in no way affected his game, if anything it seemed to improve it, but it somehow made you an even worse player. Dean was constantly laughing at how bad you were doing since it was strip pool, he couldn’t even help you out, not that he really wanted to. So, here you were bending over the table in just your tank top and a thong. Dean was unable to keep his eyes off your ass, he had only lost one item, his shirt and was only in his jeans. The only reason he had lost any clothes at all was that seeing you lose your clothing in front of him was beyond distracting and he couldn’t concentrate on the game.

“Ugh!” You groaned as you missed the hole again and finally removed your top. Leaving Dean speechless as you seemed to have forgotten you weren’t wearing a bra underneath.

“Damn” he whispered, he couldn’t keep his eyes off of you. Little did he know you had planned this out and purposely didn’t wear a bra to get him to make a move, you were tired of this will they/ won’t they game and decided to end it once and for all.

“Your turn Dean.” You say looking into his eyes. He blinked realizing you were speaking to him and moved closer to you, not caring anymore about the game. He kept approaching you until your back was up against the table. Looking up into his eyes, he growled and took your lips in his, causing you to moan and rest your hands on his chest, feeling his muscles.

Dean grabbed your hair with one hand and your waist with the other, giving a quick squeeze before he moved both hands to your waist and ripped at your thong. Taring it and discarding it before lifting you up onto the table. 

Giving you one last kiss he started making his way down your throat. Leaving little nips here and there, going lower until he reached to take a nipple in his mouth. Causing you to moan, leaning your head back and arching your chest into him, he trails his fingers up and down your waist as he plays with the other nipple. Before he descends lower and lower until he reaches your soaked core. Breathing it in before flicking his tongue over your clit slowly. You groan and grab a fistful of Dean’s har, causing him to let out a groan as well.

“Fuck baby you taste so sweet! I could spend all night here” He said as he kept licking at your core.

“Fuck Dean!” You moan out.

“That’s it, baby.” He said inserting a finger inside you as he gives kitten licks to your clit. You whimper at the sudden intrusion but pretty soon you’re grinding down onto his finger. Fucking yourself on it as he licks you, every so often giving little nips to your clit.

“Please” You beg

“Please what, baby, tell me what you want.” He tells you adding another finger. You moan and say “Fuck me, Dean, please make me cum on your tongue”

Grinning Dean moves his fingers faster inside you as he starts sucking on your clit. The added pressure makes you throw your head back in a silently scream, clamping your legs around his head. You begin shaking, soaking his face. He licks you softly through it as your legs tremble around his head.

“You ok?” He asks sweetly looking up at you, your head was still thrown back, but your breathing was finally calming down.

“I’ll tell you when I can feel my legs.” You say moving your head to smile down at him. He grins giving your clit one last kiss, causing you to jolt a little at the overstimulation. Chuckling as he stands up to give you a kiss. You moan at the taste of yourself on his tongue and grab his hips pulling him closer.

“I’ve always wanted to do that.” He said happily, you grin and nod into his chest.

“You know there are a few things I’ve always wanted to try too.” You tell Dean very seriously. He smirks and stares down at you, lifting up his eyebrow “Really? What kind of things?”

You put your arms around his neck, grabbing onto the back of his hair and playing with it “It’s best if I show you”

He grins and picks you up, throwing you over his shoulder, causing you to let out an involuntary squeal. He laughs slapping your bare ass and heading towards his room. You laugh knowing this was only going to get better.

\-----

“So, you really think this is a good idea?” Sam asked, the three of you were taking a small break before looking for a new hunt, so you were in the pool table room planning to go up against Dean. He looked very doubtful that you could win against Dean, but he didn’t know how to tell you that you sucked at playing pool. He knew Dean had been trying to teach you, but seeing as he only ever heard moans when you practiced, he doubted any real learning was getting done. 

“Yes! I’m getting better! I want to do it!” You tell him, looking to Dean for support. You had wanted to show them your skills and win the bet against Dean in doing so. The two of you couldn’t agree on where to go on vacation. You wanted the beach, but he wanted to go to a cabin and spend every day in bed with you. So the two of you had made a bet that if he won you would go to the cabin and he could pick your outfits the whole week you were there, but if you won he had to go to the beach with you and let you drive Baby for a week. You knew he wouldn’t agree to let you choose his outfits for the week, so you hadn’t brought it up in the original bet, but you knew you’d convince him sooner or later. Sam was there to make sure no one cheated, and he wanted you both gone as he had walked in on you two, one too many times. They both knew it wasn’t a real competition though as you sucked at playing, they just didn’t want to hurt your feelings. Dean especially was so in love with you, he just nodded in agreement not being able to break your heart with the truth and hurt your feelings. You made him promise not to go easy on you, but the bet had ensured he wouldn’t.

“I’m still going to win baby.” Dean said wanting to see you in a naughty little nurse getup. You grinned and walked over to the pool table and sharpened your stick.

“This is going to end badly.” Sam said, and Dean only nodded getting ready to watch you lose and play as bad as they knew you would. A few rounds of you losing and Dean was excited he was going to get you in bed all week. He had generously let you play a few rounds, feeling bad you were so bad at the game.

“Ok, boys lets try one last time. All or nothing on this game, winner for this game makes the choice and chooses what the other wears all week.” Dean’s eyebrow went up at the last part, you had never discussed you getting to dress him if you won and went to the beach. But he agreed nonetheless knowing you wouldn’t win, and he wouldn’t have to be dressed by you. He let you start, knowing he was going to win he couldn’t help but stare at your ass as you shot the ball to break, picturing all the things he was going to get you to wear for him. Missing how two stripes went in immediately, moving around the table you took your next shot, and it kept going until you only had the black ball left.

“Corner left pocket.” You said as you shot the black ball in its intended hole. Smirking because just like the rest it went in.

They were beyond shocked. Dean hadn’t even gotten to make a move, you kept making shot after shot. They couldn’t believe how good you were playing, making them question how you learned when you sucked at playing before.

“Well Dean, I believe I’ll be taking the keys to baby now.” You say smiling and turning your head innocently to the side to look at them. “Don’t worry about packing for the trip either, I already packed everything you’ll need. The speedo I bought you is going to look amazing.” Dean was in shock, staring and gaping his mouth at you, not even processing anything you said. “W-what, what just happened”

Sam burst out laughing, catching on a lot quicker than his brother “Dude, she totally played you”

You winked at Dean and grabbed the keys from his jeans as Sam left the room, still laughing as he realized what you had done. Giving Dean a kiss on the cheek, you moved to go see your new ride for the week. Before you could leave, Dean reacted and grabbed your hand, turning you around to face him.

“You little con artist. You were playing me since the beginning” Dean said a little in awe of you and a lot turned on by you.

“I had to get you to admit your feelings for me somehow” You shrugged, trying to hide the big smile on your face. He laughed, pulling you in until you were against his chest and wrapped in his arms, leaning in to give you a kiss.

“Now what were you saying about a speedo?” Dean looked down at you a little scared, you just smiled up at him. 

The beach was going to be a good time.


End file.
